America's Prettiest Towns

John Giuffo
, ContributorI travel, I look for good food when I do, and I write about both.Opinions expressed by Forbes Contributors are their own.

Cooperstown, N.Y.

Mention Long Island to most people and shoreline McMansions and celebrity-studded soirees in the Hamptons may come to mind, or acres of suburban tract housing dotted by strip malls.

But hidden away at the tip of the North Fork, far from the famous and the fatuous, is a town that perfectly mixes unpretentious Americana with the trappings of the modern food and wine scene. Landing a spot on our list of prettiest places, Greenport is perhaps Long Island’s most attractive locale--quaint summer cottages push up against old-school seafood shacks and fancy restaurants (the inventive seafood options at The Frisky Oyster never disappoint), with beach and boating options never more than ten minutes away.

“Things are much more low-key along the Peconic Bay on the North Fork,” says Jason Clampet, online editor at Frommer’s.com. “Although Manhattanites have brought art galleries and coffeeshops with them, Greenport's small inns, pebbly beaches, and fishing heritage still cater to visitors who'd rather relax than star-gaze.”

Working with travel experts from Frommer’s, Rough Guides and Midwestern Living magazine, we’ve pulled together a list of some of America’s prettiest, most enchanting towns. We looked for places that offer not only aesthetic bounty, but memorable activities and destinations nearby.

Day-trippers from New York City who aren't in the mood for a sun-and-surf-drenched weekend might prefer Cooperstown in upstate New York. “There’s lots of period architecture, there’s a little bustle trolley that runs around the town, and you’ve got the whole natural vista of the Catskills,” says Nick Edwards, an author for Rough Guides who has written about nearly every U.S. state. “It’s not touristic in any sort of tacky way.”